Sissy Men Serving Mistresses and Masters

Dear Enslaved,
Always being the dominant one in a relationship, I was drawn to Ned because of his placid manner and almost feminine face and figure. At first, he went along with being tied up for sex and often being kept that way for hours. He even shaved his scant body hair when I said I liked smooth bodies.
Next I put him to my final test and dared him to go for a walk one night in complete drag. He was intrigued and after a bit of cajoling let me put him in brief black lingerie, short black rubber latex dress, long gloves, stay-up nylons, and 4” stiletto pumps. I made up his face and placed a dark page-boy wig on his head. We were both turned on by his very feminine image in the full-length mirror. He suddenly got cold feet at the front door, but I solved that by tying his wrists behind him and draping a coat about his shoulders, then shoving his helpless, feminized body out into the hall.
It was a delightful evening. No one was in the elevator or lobby, and on the street we received admiring glances from the few people we passed. We returned horny and had sex; Ned stayed tied and feminized the whole night. From then on he was hooked. He was bound and feminized on almost every date, and soon we began living together in a small house with a large, high-fenced yard for privacy. We ordered clothes and articles from your Transvestite and other she-male catalogs and Ned wore several changes a day. I had a high paying job and good investments so I convinced Ned to quit his job and do all the womanly things around the house. He was thrilled to do so, as he was then able to stay feminized all the time.
Ned did the cleaning and cooking in either a French maid uniform and 4” to 7” stilettos or a pink or satin locking sissy maids bondage uniform, ruffled socks and Mary Janes or Sylvia Doll Shoes, and always penis gagged and in chains and leather wrist and ankle cuffs. He also wore schoolgirl outfits, gowns, velvet dresses, leopard outfits, skirts, tops and hosiery, lingerie, etc. It was such fun to tie and gag him looking like a sexy socialite, French or sissy maid, school girl in penny loafers, or a leopard bikini-clad jungle girl a la ‘5Os bondage model icon Betty Page. He used your feminizing creams and pills and even slept tied up in a corset and stiletto heels, to nip in his waist, to give his hips and butt a rounder shape tone his leg and calf muscles and ankles, and raise his high arches.
Our bliss was shattered when Ned discovered that his dick and balls were shrinking while his breasts grew, his skin became softer, his hair more silky, and his body hair disappeared. He loved being a TV bondage slave, content to receive a blowjob or handjob instead of actual intercourse in exchange for eating and finger-fucking my cunt while in bondage – but he drew the line at becoming a limp-donged, actual she-male! I was set on him being one, as he’d never been a great lay. He was in chains and a brief French maid uniform with 7” heels, and was no match for me. I knocked him out with an uppercut, and he woke to find he was tied in a compact ball, a jaw-creaking penis gag in his mouth and a huge, humming vibrator fucking his ass at its highest speed.
For three weeks I kept him tied in the spare bedroom in every muscle-straining position I could conceive, lashed him with whips and belts, walked on him in 7” stilettos, and screwed his asshole good with the vibrator, plastic and rubber dildos and my various stilettos, which he sucked clean. Ned wisely gave in, and I increased the hormone creams and tablets. He was given female behavior lessons and lashed whenever he messed up. His dwindling prick was locked in a Phallic Fidelity Enforcer, and later in a FL3C Frenum Chastity that prevented a hard-on with heavy pain. At last his breasts had large implants and his small cock was locked permanently in a FL2C Frenum, and Ned forever became “Nan,” a gorgeous, submissive, sissy she-male slave/slut.
I take bound Nan with me on those occasions I get an itch that can only be scratched by a man’s prick. Tied and gagged as a French or sissy maid, schoolgirl or naked beauty in 7” stiletto sling-backs and imitation pussy hiding her metal-encased tiny cock, she watches me get what she can no longer give me. Mistress Elga